Cheap flights from MDW to SAN (Midway Intl. to San Diego Intl.)

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Cheap Flights from MDW to SAN starting at $74 One Way, $148 Round Trip

Prices starting at $148 for return flights and $74 for one-way flights to San Diego Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jun 22 - Mon, Jun 24
MDW
Chicago
SAN
San Diego
$148 Roundtrip, found 12 hours ago
$148
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Sat, Jun 22 from Chicago to San Diego, returning Mon, Jun 24, priced at $148 found 12 hours ago
Tue, Aug 13 - Sat, Aug 17
MDW
Chicago
SAN
San Diego
$150 Roundtrip, found 1 hour ago
$150
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Aug 13 from Chicago to San Diego, returning Sat, Aug 17, priced at $150 found 1 hour ago
Sat, Aug 17 - Mon, Aug 19
MDW
Chicago
SAN
San Diego
$158 Roundtrip, found 5 days ago
$158
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 17 from Chicago to San Diego, returning Mon, Aug 19, priced at $158 found 5 days ago
Tue, Sep 17 - Thu, Sep 19
MDW
Chicago
SAN
San Diego
$166 Roundtrip, found 6 days ago
$166
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Sep 17 from Chicago to San Diego, returning Thu, Sep 19, priced at $166 found 6 days ago
Wed, Jun 26 - Thu, Jul 11
MDW
Chicago
SAN
San Diego
$168 Roundtrip, found 7 hours ago
$168
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Jun 26 from Chicago to San Diego, returning Thu, Jul 11, priced at $168 found 7 hours ago

Hotel Ideas near San Diego Intl.

Airport Hotels near San Diego Intl.

Wyndham Garden San Diego Near SeaWorld
Wyndham Garden San Diego Near SeaWorld
3 out of 5
3737 Sports Arena Blvd, San Diego, CA
The price is $139 per night from Jun 11 to Jun 12
$139
per night
Jun 11 - Jun 12
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff ...
7/10 Good! (2,764 reviews)
"Nice stay"

Reviewed on Jun 10, 2024

Wyndham Garden San Diego Near SeaWorld
Sheraton San Diego Hotel and Marina
Sheraton San Diego Hotel and Marina
4 out of 5
1380 Harbor Island Dr, San Diego, CA
The price is $194 per night from Jun 23 to Jun 24
$194
per night
Jun 23 - Jun 24
Book a stay at this business-friendly hotel in San Diego. Enjoy 3 outdoor pools, 6 restaurants, and a marina. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (2,301 reviews)
"We are pleased with our stay. Very nice and clean room with spectacular views!!"

Reviewed on Jun 9, 2024

Sheraton San Diego Hotel and Marina
Wyndham San Diego Bayside
Wyndham San Diego Bayside
4 out of 5
1355 N Harbor Drive, San Diego, CA
The price is $178 per night from Jun 17 to Jun 18
$178
per night
Jun 17 - Jun 18
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the restaurant and the ...
8/10 Very Good! (5,955 reviews)
"Nice views"

Reviewed on Jun 10, 2024

Wyndham San Diego Bayside
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In San Diego

Wyndham Garden San Diego Near SeaWorld
Wyndham Garden San Diego Near SeaWorld
3 out of 5
3737 Sports Arena Blvd, San Diego, CA
The price is $139 per night from Jun 11 to Jun 12
$139
per night
Jun 11 - Jun 12
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff ...
7/10 Good! (2,764 reviews)
"Nice stay"

Reviewed on Jun 10, 2024

Wyndham Garden San Diego Near SeaWorld
Wyndham San Diego Bayside
Wyndham San Diego Bayside
4 out of 5
1355 N Harbor Drive, San Diego, CA
The price is $178 per night from Jun 17 to Jun 18
$178
per night
Jun 17 - Jun 18
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the restaurant and the ...
8/10 Very Good! (5,955 reviews)
"Nice views"

Reviewed on Jun 10, 2024

Wyndham San Diego Bayside
Paradise Point Resort & Spa
Paradise Point Resort & Spa
4 out of 5
1404 Vacation Rd, San Diego, CA
The price is $283 per night from Jun 11 to Jun 12
$283
per night
Jun 11 - Jun 12
Book a stay at this beach resort in San Diego. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in ...
8.4/10 Very Good! (1,846 reviews)
Peaceful, Relaxing, and Friendly resort
"I went with a friend to spend a few days relaxing and getting spa treatments. We had a bungalow near the center of the complex, and everything (beach, restaurants, spa, market, pools, lobby) was very convenient. The resort was built in 1962, but has been kept up very well. Everything is clean, the ..."

Reviewed on Jun 10, 2024

Paradise Point Resort & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

San Diego Hotels With Airport Transportation

Holiday Inn Express San Diego Airport - Old Town, an IHG Hotel
Holiday Inn Express San Diego Airport - Old Town, an IHG Hotel
2.5 out of 5
1955 San Diego Ave, San Diego, CA
The price is $171 per night from Jun 16 to Jun 17
$171
per night
Jun 16 - Jun 17
Book a stay at this business-friendly hotel in San Diego. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
8.8/10 Excellent! (1,119 reviews)
"I like that it was close by convenient from the airport. Room is clean. A bit noisy close to the highway."

Reviewed on Jun 7, 2024

Holiday Inn Express San Diego Airport - Old Town, an IHG Hotel
Wyndham San Diego Bayside
Wyndham San Diego Bayside
4 out of 5
1355 N Harbor Drive, San Diego, CA
The price is $178 per night from Jun 17 to Jun 18
$178
per night
Jun 17 - Jun 18
Book a stay at this business-friendly hotel in San Diego. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the restaurant and the ...
8/10 Very Good! (5,955 reviews)
"Nice views"

Reviewed on Jun 10, 2024

Wyndham San Diego Bayside
Sheraton San Diego Hotel and Marina
Sheraton San Diego Hotel and Marina
4 out of 5
1380 Harbor Island Dr, San Diego, CA
The price is $194 per night from Jun 23 to Jun 24
$194
per night
Jun 23 - Jun 24
Book a stay at this business-friendly hotel in San Diego. Enjoy 3 outdoor pools, 6 restaurants, and a marina. Our guests praise the helpful staff and the clean ...
7.6/10 Good! (2,301 reviews)
"We are pleased with our stay. Very nice and clean room with spectacular views!!"

Reviewed on Jun 9, 2024

Sheraton San Diego Hotel and Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced San Diego Hotels

E-Z 8 Motel Old Town
E-Z 8 Motel Old Town
2.5 out of 5
4747 Pacific Highway, San Diego, CA
The price is $94 per night from Jun 11 to Jun 12
$94
per night
Jun 11 - Jun 12
Book a stay at this business-friendly hotel in San Diego. Enjoy free parking, WiFi (surcharge), and a 24-hour front desk. Our guests praise the helpful staff ...
5.8/10 (2,056 reviews)
"It was comfortable"

Reviewed on Jun 8, 2024

E-Z 8 Motel Old Town
Pleasant Inn
Pleasant Inn
2.5 out of 5
5550 Clairemont Mesa Blvd, San Diego, CA
The price is $140 per night from Jun 11 to Jun 12
$140
per night
Jun 11 - Jun 12
Stay at this hotel in San Diego. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.2/10 Very Good! (1,023 reviews)
"The room and the hotel were very clean. Everything in the room functioned as it should. Things were quiet. I was pleased with the value and the quality of the property."

Reviewed on Jun 9, 2024

Pleasant Inn
Kings Inn San Diego
Kings Inn San Diego
2.5 out of 5
1333 Hotel Cir S, San Diego, CA
The price is $107 per night from Jun 12 to Jun 13
$107
per night
Jun 12 - Jun 13
Stay at this hotel in San Diego. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (2,746 reviews)
Nice place to stay
"Right off the highway with easy access. Nice place to stay and not far from zoo/ Balboa Park or Old Town or downtown."

Reviewed on Jun 10, 2024

Kings Inn San Diego
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in San Diego

The Dana on Mission Bay
The Dana on Mission Bay
3.5 out of 5
1710 W Mission Bay Dr, San Diego, CA
The price is $179 per night from Jun 11 to Jun 12
$179
per night
Jun 11 - Jun 12
Book a stay at this family-friendly hotel in San Diego. Enjoy 2 outdoor pools, a marina, and 2 spa tubs. Our guests praise the breakfast and the pool in our ...
8.6/10 Excellent! (2,553 reviews)

Families like: Outdoor pools, playground, close to beach, extra beds/cribs

Travelers say...
"Good"

Reviewed on Jun 9, 2024

The Dana on Mission Bay
Bahia Resort Hotel
Bahia Resort Hotel
3.5 out of 5
998 W Mission Bay Dr, San Diego, CA
The price is $249 per night from Jun 12 to Jun 13
$249
per night
Jun 12 - Jun 13
Book a stay at this beach resort in San Diego. Enjoy free parking, a beach locale, and a marina. Our guests praise the pool and the restaurant in our reviews. ...
8.4/10 Very Good! (1,324 reviews)

Families like: Outdoor pools, game room, on the beach, outdoor tennis courts

Travelers say...
"Room was great, but very noisy from sounds of outside deliveries etc Beautiful balcony and view, but hard to enjoy with the smokers below us"

Reviewed on Jun 8, 2024

Bahia Resort Hotel
Catamaran Resort and Spa
Catamaran Resort and Spa
4 out of 5
3999 Mission Boulevard, San Diego, CA
The price is $259 per night from Jun 11 to Jun 12
$259
per night
Jun 11 - Jun 12
Book a stay at this beach resort in San Diego. Enjoy free WiFi, a full-service spa, and a beach locale. Our guests praise the restaurant and the helpful staff ...
7.6/10 Good! (1,108 reviews)

Families like: Outdoor pools, game room, on the beach, bicycle rentals

Travelers say...
"Always great!"

Reviewed on Jun 6, 2024

Catamaran Resort and Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Map To Nearby Hotels

MDW to SAN Route Info

Origin Airport
Chicago
Destination Airport
San Diego
Number Of Airlines Serving
1
Distance
1725 mi
Shortest Flight Departure Time
5:10AM CDT
Shortest Flight Departure Date
Jun 17
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
SAN Address & GPS
Address:
Airport Drive
San Diego CA, 92101
United States
IATA Code:
SAN
Longitude:
-117.197312
Latitude:
32.731938
Time Zone:
America/Los_Angeles

Frequently asked questions

Am I able to catch a flight from Chicago, IL Airport (MDW-Midway Intl.) to San Diego, CA Airport (SAN-San Diego Intl.) now?
Our Covid-19 Travel Advisor can help you with questions about travel restrictions and quarantine requirements when flying from Chicago, IL Airport (MDW-Midway Intl.) to San Diego, CA Airport (SAN-San Diego Intl.).
Are there non-stop flights from MDW to San Diego Intl. Airport (SAN)?
Forget about annoying stopovers or missing a connecting flight. Southwest Airlines will fly you directly from MDW to SAN.
What is the shortest flight from Chicago Airport to San Diego Airport?
The quickest flight from West Lawn to Leucadia is around 4 hours and 15 minutes. Order your favorite tipple from the cabin crew, hone your travel itinerary or get to know your neighbors — you’ll have the time on this medium-haul trip.
How many hours flight from Chicago Airport to San Diego, CA Airport (SAN-San Diego Intl.)?
The journey from Midway Intl. Airport (MDW) to San Diego Intl. Airport (SAN) will take an average of 4 hours and 18 minutes. A couple of good movies, a gripping novel and a decent snooze will make the time zoom by.
If I am not able to travel due to COVID-19, can I cancel my flight to San Diego, CA Airport (SAN-San Diego Intl.)?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to San Diego, CA Airport (SAN-San Diego Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to San Diego, CA Airport (SAN-San Diego Intl.) with flexible change policies?
In most cases you’ll have the option to reschedule your flight to San Diego, CA Airport (SAN-San Diego Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What airlines have the most flights from Chicago Airport to San Diego Intl. Airport (SAN)?
If you want a worry-free flight, reserve your ticket with Southwest Airlines. This air carrier has 156 flights each month from Chicago, IL Airport (MDW-Midway Intl.) to San Diego Intl. Airport (SAN) and is one of the most popular airlines servicing this route.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.